Kelley Systems Group Technology leadership for growing companies

About

Caleb J. Kelley

I am usually the first real technology leader a growing company works with. Having already held that seat through the exact growth stage our clients are entering, I know what the next two years ask of a business before it gets there.

Background

I joined a private aviation and travel company in operations. It had almost no operational data. I proposed the Salesforce platform it now runs on, built it, and trained every employee on it.

When the VP of Engineering left, I took on his work after a single one-hour handoff and expanded the charter to cover every system in the company. Over eight and a half years and three promotions I built business intelligence and engineering into standalone departments, developed the leader for each one internally, and handed both functions off. I stood up an engineering team in Bangalore, traveling there three times to train the engineers in person. I led the company's adoption of AI, including an enterprise agreement for Claude and a hybrid on-premise and cloud inference stack.

I kept consulting clients on the side through all of it, most of them for about four years. By 2026 the practice had outgrown what a side commitment could serve, so it went full time.

Strategy and build, same person

Strategy on Monday, building in the platform on Tuesday. Not a strategist who hands over a deck and leaves, and not an administrator waiting on tickets. The value sits in one person deciding what should happen and then making it happen.

Delegate and elevate

I work the EOS model deliberately. Build the capability, develop a successor, hand it off. I have done it twice with named successors. An engagement leaves a company with capable, confident people running what we built together.

On tools

I spent years under a mandate to prevent platform sprawl while the company grew sixfold. Consolidating and integrating beats adding. The answer to most problems is a system already paid for, used properly.

Scope and scale

6
Engineers led, split between the US and Bangalore
$300K
Annual systems budget owned, with every vendor contract
4
Offices worldwide supported
40 of 200
Candidates personally interviewed to build the India team
2022
Awarded the company's highest honor

Client work

Current engagements, most of them running about four years. Client names stay private here, and I am glad to discuss specifics and provide references in a conversation.

Salesforce and Certinia platform ownership for a contractor-heavy services firm

A small internal team supports several hundred field contractors nationwide. We own platform strategy, and I engage the COO directly on technology questions that reach beyond the platform.

  • Migrated the org from Classic to Lightning.
  • Consolidated legacy Process Builder workflows into Flows, improving backend performance across a fragmented environment.

Salesforce strategy and advisory to a Chief Revenue Officer

Began as platform work and now reaches technology problems across the business.

  • Extended an out-of-the-box org with custom objects for customer setup.
  • Built reporting and dashboards where there had been no visibility.
  • Trained users directly to drive adoption.

End-to-end management of a business-critical Salesforce environment

  • Custom Flows, Apex development, and Zapier automations.
  • Shifted the engagement from reactive requests to proactive roadmap ownership, governance, and stakeholder reviews.

Track record

The company grew from 15 employees post-pandemic to roughly 100, and from $18M to $50M in projected revenue. I was promoted three times across that period and awarded its highest honor in 2022.

Platform and data

  • Proposed and implemented Salesforce end to end, replacing a near-total absence of operational data with real-time reporting across four offices.
  • Migrated years of reservation and revenue history out of accounting spreadsheets into custom objects, making it operational rather than archival.
  • Built executive dashboards used in leadership review, and departmental reporting that ended the queue of report requests.
  • Built 100+ automated Flows, with Apex where declarative configuration could not reach.

Teams and leadership

  • Created the business intelligence capability, developed its leader from zero Salesforce experience through Administrator certification, and spun the function off as its own department.
  • Developed a junior engineer into the lead now being promoted to Director of Engineering.
  • Established an offshore engineering team in Bangalore, traveling there three times to train engineers in person.
  • Designed a Salesforce-based QA process that made a structured intern program possible, now staffing five to seven interns at a time.

Systems and cost discipline

  • Executed a COO mandate to prevent platform sprawl while the company grew sixfold, consolidating and integrating rather than adding tools.
  • Integrated Asana, Slack, Salesforce, and the in-house Rails platform through Zapier to eliminate duplicate entry.
  • Built the IT support intake workflow with SLAs and scorecard metrics where no measurement existed.
  • Automated the monthly profit-share close so every employee's payout was accurate.

AI, applied

  • Led company-wide AI adoption, including an Anthropic enterprise agreement for Claude.
  • Integrated AI assistance into Slack and engineering workflows.
  • Built a hybrid on-premise and cloud inference stack blending open-weight and frontier models.
  • Held IT headcount flat against a workload that would justify a third hire, using AI to absorb the growth instead of adding salary.

Capabilities

Leadership

  • IT and engineering department leadership
  • Distributed and offshore teams
  • Strategy and budget ownership
  • Hiring and talent development
  • Vendor management, SOPs, SLAs
  • EOS

Salesforce and data

  • Platform ownership and architecture
  • Flow automation and Apex development
  • Classic-to-Lightning migration
  • Sandbox-to-production release management
  • Data governance and migration
  • Reporting, dashboards, KPI design

Systems and AI

  • System architecture and integration
  • Platform consolidation
  • Enterprise AI adoption and LLM integration
  • Hybrid on-premise and cloud inference
  • Zapier, Certinia, Jamf, Jira, Asana
  • Google Workspace, Slack, 1Password
Where we work

Upstate South Carolina and the Southeast, close enough to be in the room when it matters. Remote engagements work too, and have for four years. One client has been in Denver the whole time.